title: Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3.
abstract: An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl3 is highly diastereoselective. 2,2-Di-substituted cyclization products were obtained in good to excellent yields.
authors.affiliation: Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China.
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Ma
authors.forename: Qin
authors.initials: Q
authors.lastname: Tang
authors.forename: Jun
authors.initials: J
authors.lastname: Ke
authors.forename: Jichao
authors.initials: J
authors.lastname: Zhang
authors.forename: Cong
authors.initials: C
authors.lastname: Wang
authors.forename: Haibo
authors.initials: H
authors.lastname: Wang
authors.forename: Yuxue
authors.initials: Y
authors.lastname: Li
authors.forename: Huawu
authors.initials: H
authors.lastname: Shao
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001729:Bismuth / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D002241:Carbohydrates; D002712:Chlorides; D005663:Furans; D011714:Pyrans; C534543:bismuth trichloride; D001729:Bismuth; C039281:furan